Search Results (55)

This study investigated the neuroprotective activity of oligomeric stilbenes (OSs) derived from Alpha grape stems in various in vitro models of Parkinson’s disease (PD). Using neurotoxin-induced cellular models, including 1-methyl-4-phenylpyridine (MPP+), paraquat (PQ), 6-hydroxydopamine (6-OHDA), and rotenone, we screened the cytoprotective effects of ampelopsin A (1), ε-viniferin (2), vitisin D (3), vitisin A (4), α-viniferin (5), trans-vitisin B (6), cis-vitisin B (7), and melanoxylin A (8). The results demonstrate that certain stilbenes significantly enhanced cell viability and reduced reactive oxygen species (ROS) levels in neurotoxin-treated Neuro-2a cells. Notably, vitisin A and trans-vitisin B exhibited promising neuroprotective properties by decreasing mitochondrial ROS and cardiolipin peroxidation. This study highlights the potential of these compounds in mitigating oxidative stress and inflammation associated with PD. Additionally, we provided new insights into the antioxidant mechanisms of these stilbenes, including their direct ROS-scavenging abilities. Our findings contribute to the understanding of oligomeric stilbenes as potential therapeutic agents for the prevention and treatment of neurodegenerative diseases, particularly those associated with oxidative damage. Further research is warranted to explore its clinical applications and underlying mechanisms of action. Full article

Soil mulching is a useful agronomic practice that promotes early fruit maturation and affects fruit quality. However, the regulatory mechanism of fruit metabolites under soil-mulching treatments remains unknown. In this study, variations in the gene sets and metabolites of grape berries after mulching (rice straw + felt + plastic film) using transcriptome and metagenomic sequencing were investigated. The results of the cluster analysis and orthogonal projection to latent structures discriminant analysis of the metabolites showed a difference between the mulching and control groups, as did the principal component analysis results for the transcriptome. In total, 36 differentially expressed metabolites were identified, of which 10 (resveratrol, ampelopsin F, piceid, 3,4′-dihydroxy-5-methoxystilbene, ε-viniferin, trans resveratrol, epsilon-viniferin, 3′-hydroxypterostilbene, 1-methyl-resveratrol, and pterostil-bene) were stilbenes. Their content increased after mulching, indicating that stilbene synthase activity increased after mulching. The weighted gene co-expression network analysis revealed that the turquoise and blue modules were positively and negatively related to stilbene compounds. The network analysis identified two seed genes (VIT_09s0054g00610, VIT_13s0156g00260) and two transcription factors (VIT_13s0156g00260, VIT_02s0025g04590). Overall, soil mulching promoted the accumulation of stilbene compounds in grapes, and the results provided key genetic information for further studies. Full article

Stilbenes in the roots of Carex acuta and Carex lepidocarpa were studied. Root samples were extracted with 100% methanol and analyzed by HPLC and LC-MS. In this way, trans-resveratrol dimers (m/z 455 Da [M + H]⁺), trimers (m/z 681 Da [M + H]⁺) and tetramers (m/z 907 Da [M + H]⁺) were identified in the extracts. Using LC-NMR in stop-flow mode, pallidol and trans-ε-viniferin as dimers were identified. After the separation of individual peaks and their measurement by ¹H NMR, cis and trans-miyabenol A as a tetramer and cis-miyabenol C as a trimer were identified. In the case of miyabenol A, it is a chromatographically inseparable mixture of cis and trans isomers in the ratio of 2:3 according to ¹H NMR measurement. In the case of cis-miyabenol C, the Z-trans-trans-miyabenol C configuration was confirmed. The remaining unidentified peak with a practically identical UV-VIS spectrum to that of cis-miyabenol C is most likely another isomer of miyabenol C. Full article

Grapevines (Vitis spp.) produce several valuable polyphenol-type secondary metabolites including various stilbenoids. Although the potential application of stilbenes may offer alternative solutions to food safety or health challenges, only little information is available on their antibacterial activity against foodborne pathogens. In this work, high-performance liquid chromatography was used to analyze the stilbenoid profile of various wild Vitis species, including V. amurensis, V. davidii, V. pentagona, and V. romanetii, selected from the gene bank for grapes at the University of Pécs, Hungary. We found that the stilbene profile of cane extracts is strongly genotype-dependent, showing the predominant presence of ε-viniferin with a wide concentration range ≈ 320–3870 µg/g dry weight. A novel yet simple and efficient extraction procedure was developed and applied for the first time on grape canes, resulting in ε-viniferin-rich crude extracts that were tested against Listeria monocytogenes, an important foodborne pathogen. After 24 h exposure, V. pentagona and V. amurensis crude extracts completely eliminated the bacteria at a minimum bactericidal concentration of 42.3 µg/mL and 39.2 µg/mL of ε-viniferin, respectively. On the other hand, V. romanetii extract with 7.8 µg/mL of ε-viniferin resulted in 4 log reduction in the viable bacterial cells, while V. davidii extract with 1.4 µg/mL of ε-viniferin did not show significant antibacterial activity. These findings indicate that the ε-viniferin content was directly responsible for the antibacterial effect of cane extract. However, pure ε-viniferin (purity > 95%) required a higher concentration (188 µg/mL) to eradicate the bacteria under the same conditions, suggesting the presence of other antibacterial compounds in the cane extracts. Investigating the onset time of the bactericidal action was conducted through a kinetic experiment, and results showed that the reduction in living bacterial number started after 2 h; however, the bactericidal action demanded 24 h of exposure. Our results revealed that the canes of V. pentagona and V. amurensis species are a crucial bio-source of an important stilbene with antimicrobial activity and health benefits. Full article

Grapevine roots, as a side-stream of a vineyard, are a sustainable resource for the recovery of oligomeric stilbenoids, such as the bioactive r-viniferin. The aim of this study is to evaluate an in silico-supported method, based on the Conductor-like Screening Model for Real Solvents (COSMO-RS), for selection of environmentally friendly natural deep eutectic solvents (NADES) with regard to the extraction of grapevine roots. The most suitable NADES system for ultrasonic-assisted extraction of r-viniferin was choline chloride/1,2-propanediol. The optimal extraction parameters for r-viniferin were determined using single-factor experiments as follows: choline chloride/1,2-propanediol 1/2 mol/mol, 10 wt% H₂O, biomass/NADES ratio 1/10 g/g, and 10 min extraction time. Under optimized conditions, the extraction yield of r-viniferin from grapevine roots reached 76% of the total r-viniferin content. Regarding stability, stilbenoids in choline chloride/1,2-propanediol remained stable during 128 days of storage at ambient temperature. However, fructose/lactic acid-based NADES were observed to degrade stilbenoids; therefore, the removal of the NADES will be of interest, with a suitable method implemented using Amberlite^® XAD-16N resin. As green solvents, the NADES have been used as effective and environmentally friendly extractants of stilbenoid-containing extracts from grapevine roots for potential applications in the cosmetic and pharmaceutical industry or as nutraceuticals in the food industry. Full article

A grapevine shoot extract (GSE) was obtained using ultrasound-assisted extraction and characterized. The main phenolic constituents were identified as stilbenoids. Among them, trans-resveratrol and trans-ε-viniferin stood out. The GSE was administered to an isoproterenol-induced myocardial injury animal model. The extract alleviated the associated symptoms of the administration of the drug, i.e., the plasma lipid profile was improved, while the disturbed plasma ion concentration, the cardiac dysfunction markers, the DNA laddering, and the necrosis of myocardial tissue were diminished. This effect could be related to the anti-oxidative potential of GSE associated with its antioxidant properties, the increased levels of endogenous antioxidants (glutathione and enzymatic antioxidants), and the diminished lipid peroxidative markers in the heart. The results also revealed angiotensin-converting enzyme (ACE)-inhibitory activity, which indicated the potential of GSE to deal with cardiovascular disease events. This work suggests that not only trans-resveratrol has a protective role in heart function but also GSE containing this biomolecule and derivatives. Therefore, GSE has the potential to be utilized in the creation of innovative functional ingredients. Full article

Salinity stress has become an increasing threat to viticulture in the Tunisian oasis, and more generally, the characterization of salinity tolerance markers can be of great interest for sustainable grape production. This study investigated some metabolic adaptations in different tissues of the ripe berries of indigenous grapevine cultivars after exposure to salt stress to identify the key traits of salt stress tolerance under oasis conditions. We especially focused on the adaptive responses occurring at the level of amino acids, polyamines, and stilbene phytoalexins in the grape berry skin, pulp, and seeds of six grapevine cultivars differing in phenotypic and ampelographic characteristics. Our data showed that amino acids accumulated strongly in the pulp and skin, while resveratrol, trans-piceid and trans-ε-viniferin, as major phytoalexins, significantly accumulated in the seeds. High salinity was also found to increase both the berry skin and pulp contents of essential amino acids such as threonine, valine, leucine, isoleucine, lysine, methionine, and phenylalanine. The amounts of stilbenes also increased under high salinity in the berry skin of all the studied cultivars. Polyamine homeostasis within the different berry tissues suggested enhanced polyamine biosynthesis rather than polyamine oxidation in response to high salinity. Our principal component analysis revealed a clear discrimination between the cultivars based on their metabolic profiles within the ripe berry tissues under high salinity. Full article

Grapevine canes are an important source of bioactive compounds, such as stilbenoids. This study aimed to evaluate an in silico method, based on the Conductor-like Screening Model for Real Solvents (COSMO-RS) to isolate stilbenoids from a grapevine cane extract by offline heart-cut high-performance countercurrent chromatography (HPCCC). For the following extraction of resveratrol and ε-viniferin from grapevine canes, natural deep eutectic solvents (NADES) were used as an environmentally friendly alternative to the traditionally used organic solvents. In order to evaluate a variety of combinations of hydrogen bond acceptors (HBAs) and hydrogen bond donors (HBDs) for the targeted extraction of stilbenoids, COSMO-RS was applied. In particular, ultrasonic-assisted extraction using a solvent mixture of choline chloride/1,2-propanediol leads to higher extraction yields of resveratrol and ε-viniferin. COSMO-RS calculations for NADES extraction combined with HPCCC biphasic solvent system calculations are a powerful combination for the sustainable extraction, recovery, and isolation of natural products. This in silico-supported workflow enables the reduction of preliminary experimental tests required for the extraction and isolation of natural compounds. Full article

In this study, we compared the polyphenolic composition of the roasted grapevine wood chips of four Vitis vinifera cultivars—namely, Sorbara, Grasparossa, Malbo Gentile, and Spergola. These waste byproducts have the potential as infusion chips for the aging of alcoholic beverages and vinegars, contributing to an enriched sensory profile. Roasting amplifies aromatic nuances and triggers the depletion of crucial bioactive compounds, including polyphenols. We investigated the extent of polyphenolic loss in the ethanolic extract of roasted grapevine chips to repurpose this waste byproduct and assess its potential. We assessed the levels of trans-resveratrol, trans-ε-viniferin, trans-piceatannol, and the main resveratrol trimer. Our findings indicated a significant decrease in polyphenol content as the roasting temperature increased, from 16.85–21.12 mg GAE/g for grapevine chips roasted at 120 °C to 3.10–7.77 mg GAE/g for those roasted at 240 °C. This study also highlights notable genotypic differences in polyphenolic content. Among the red grape cultivars analyzed, Sorbara exhibited the highest levels (7.77–21.12 mg/GAEg), whereas the white grape cultivar Spergola showed the lowest polyphenolic content (3.10–16.85 mg/GAEg). These findings not only contribute to the scientific understanding of polyphenol stability but also hold practical implications for the enhancement of aged beverages, as well as advancing sustainable practices in the viticulture industries. Full article

The control of oxidative stress with natural active substances could limit the development of numerous pathologies. Our objective was to study the antiradical effects of resveratrol (RSV), ε-viniferin (VNF), and vitisin B (VB) alone or in combination, and those of a standardized stilbene-enriched vine extract (SSVE). In the DPPH-, FRAP-, and NO-scavenging assays, RSV presented the highest activity with an IC₅₀ of 81.92 ± 9.17, 13.36 ± 0.91, and 200.68 ± 15.40 µM, respectively. All binary combinations resulted in additive interactions in the DPPH- and NO-scavenging assays. In the FRAP assay, a synergic interaction for RSV + VNF, an additive for VNF + VB, and an antagonistic for RSV + VB were observed. The ternary combination of RSV + VNF + VB elicited an additive interaction in the DPPH assay and a synergic interaction in the FRAP- and NO-scavenging assays. There was no significant difference between the antioxidant activity of the SSVE and that of the combination of RSV + VNF. In conclusion, RSV presented the highest effects, followed by VNF and VB. The interactions revealed additive or synergistic effects, depending on the combination of the stilbenes and assay. Full article

The seeds of Paeonia clusii Stern subsp. clusii and Paeonia mascula (L.) Mill. subsp. mascula growing wild in Greece, though not previously investigated, has been studied as a source of bioactive stilbenoids and other phenolics. Their methanol extracts were analyzed using ultra high-performance liquid chromatography—high-resolution mass spectrometry (UHPLC-HRMS), and among the identified metabolites (62), 19 paeoniflorin’s derivatives, 17 flavonoids and 12 stilbenes were detected. Moreover, through classic phytochemical separation procedures, twelve among them were isolated and fully spectrally determined as trans-resveratrol, trans-resveratrol-4′-O-β-D-glucopyranoside, cis-resveratrol-4′-O-β-D-glucopyranoside, trans-gnetin-H, trans-ε-viniferin, luteolin, luteolin-3′-O-β-D-glucopyranoside, luteolin-3′,4′-di-O-β-D-glucopyranoside, apigenin, hispidulin, paeoniflorin and benzoyl-paeoniflorin. All seed extracts were measured for their total phenolic content (TPC), appearing as a rich source (116.04 and 103.63 mg GAE/g extract, respectively), followed by free radical (DPPH) scavenging capacity (75.24% and 91.54% inhibition at the concentration of 200 μg/mL). The evaluation of tyrosinase inhibition for both extracts (61% and 70%, respectively) confirmed the potential for their future application in skin health care, comparable with other paeonies of Chinese origin, which are well-known as skin whitening and anti-aging promoters. Full article

A new oligostilbene trimer, malaysianol F (1), together with ten known stilbenes (2–11), were successfully separated and purified from the acetone extract of the lianas of Gnetum microcarpum. Malaysianol D (2) was isolated for the first time in Gnetum plants. The tanninless crude extract (52.5 g) was fractionated using a vacuum liquid chromatography (VLC) technique to give five major fractions. Fraction 2 (4.68 g), 3 (4.79 g) and 4 (9.29 g) were all subjected to further isolation and purification using VLC, column chromatography (CC) and repetitive radial chromatography (RC) techniques with the best solvent system to yield malaysianol F (1) (6.2 mg), malaysianol D (2) (62.5 mg), malaysianol E (3) (2.4 mg), ε-viniferin (4) (10 mg), resveratrol (5) (6.5 mg), gnetol (6) (3.5 mg), gnetucleistol C (7) (12.2 mg), isorhapontigenin (8) (8 mg), cuspidan B (9) (3.2 mg), parvifolol D (10) (4.8 mg) and gnetifolin M (11) (2.5 mg). Their structures were determined on the basis of the analysis of spectral evidence by extensive NMR data analyses and comparison with the related published data. Several compounds were tested for anti-inflammatory activity. Their inhibitory effect on Prostaglandin E₂ (PGE₂) was tested using radioimmunoassay techniques. Compound 6 exhibited significant concentration-dependent inhibitory effects on PGE₂ production with IC₅₀ values of 1.84 µM comparable with the positive control, indomethacin (IC₅₀ 1.29 µM). Full article

α-Viniferin, a natural stilbene compound found in plants and a polymer of resveratrol, had demonstrated potential anti-cancer and anti-inflammatory effects. However, the specific mechanisms underlying its anti-cancer activity were not yet fully understood and required further investigation. This study evaluated the effectiveness of α-viniferin and ε-viniferin using MTT assay. Results showed that α-viniferin was more effective than ε-viniferin in reducing the viability of NCI-H460 cells, a type of non-small cell lung cancer. Annexin V/7AAD assay results provided further evidence that the decrease in cell viability observed in response to α-viniferin treatment was due to the induction of apoptosis in NCI-H460 cells. The present findings indicated that treatment with α-viniferin could stimulate apoptosis in cells by cleaving caspase 3 and PARP. Moreover, the treatment reduced the expression of SIRT1, vimentin, and phosphorylated AKT, and also induced AIF nuclear translocation. Furthermore, this research provided additional evidence for the effectiveness of α-viniferin as an anti-tumor agent in nude mice with NCI-H460 cell xenografts. As demonstrated by the TUNEL assay results, α-viniferin promoted apoptosis in NCI-H460 cells in nude mice. Full article

This review refers to botanical, ecological and phytochemical characteristics of Vitis vinifera L. (vine grape)–a species, the valuable properties of which are widely exploited in the food industry and in recent times in medicine as well as in phytocosmetology. The general characteristic of V. vinifera, followed by the chemical composition and biological activities of different extracts obtained from the plant (fruit, skin, pomace, seed, leaf and stem extracts), are provided. A concise review of the extraction conditions of grape metabolites and the methods of their analysis are also presented. The biological activity of V. vinifera is determined by the presence of high contents of polyphenols, mainly flavonoids (e.g., quercetin, kaempferol), catechin derivatives, anthocyanins and stilbenoids (e.g., trans-resveratrol, trans-ε-viniferin). The review pays particular attention to the application of V. vinifera in cosmetology. It has been proven that V. vinifera possesses strong cosmetological-related properties, such as anti-ageing properties, anti-inflammatory properties and skin-whitening properties. Moreover, a review of studies on V. vinifera biological activities, which are of particular interest for dermatologic problems, are disclosed. Furthermore, the work also emphasises the importance of biotechnological studies on V. vinifera. The last part of the review is addressed to the safety of the use of V. vinifera. Full article

In this study, the black fertile (BSs) and the red unfertile seeds (RSs) of the Greek endemic Paeonia clusii subsp. rhodia (Stearn) Tzanoud were studied for the first time. Nine phenolic derivatives, trans-resveratol, trans-resveratrol-4′-O-β-d-glucopyranoside, trans-ε-viniferin, trans-gnetin H, luteolin, luteolin 3′-O-β-d-glucoside, luteolin 3′,4′-di-O-β-d-glucopyranoside, and benzoic acid, along with the monoterpene glycoside paeoniflorin, have been isolated and structurally elucidated. Furthermore, 33 metabolites have been identified from BSs through UHPLC-HRMS, including 6 monoterpene glycosides of the paeoniflorin type with the characteristic cage-like terpenic skeleton found only in plants of the genus Paeonia, 6 gallic acid derivatives, 10 oligostilbene compounds, and 11 flavonoid derivatives. From the RSs, through HS-SPME and GC-MS, 19 metabolites were identified, among which nopinone, myrtanal, and cis-myrtanol have been reported only in peonies’ roots and flowers to date. The total phenolic content of both seed extracts (BS and RS) was extremely high (up to 289.97 mg GAE/g) and, moreover, they showed interesting antioxidative activity and anti-tyrosinase properties. The isolated compounds were also biologically evaluated. Especially in the case of trans-gnetin H, the expressed anti-tyrosinase activity was higher than that of kojic acid, which is a well-known whitening agent standard. Full article